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Vacation Rentals in Kailua, HI

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All 103 Rentals in Kailua
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From
$199
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
15 photos Details Reviews (1) Make Inquiry
From
$179
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
21 photos Details Reviews (2) Make Inquiry
From
$139
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
7 photos Details Reviews (1) Make Inquiry
Also consider
Kailuana Hale
4 Bedrooms, sleeps 8
$550 - $825 / night
Hale Ainoni
3 Bedrooms, sleeps 6
$450 - $650 / night
Kaapuni Kainani
3 Bedrooms, sleeps 8
$475 - $950 / night
Step Out Your Door to the Sand at Makaha!
1 Bedroom, sleeps 4
$90 / night
From
$126
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
16 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed July 7, 2014
We enjoyed staying in this neat and clean studio apartment. Sabine and Ray were welcoming and have put a lot of thought into providing everything for guests' comfort. We loved...
4 of 5 stars Reviewed June 28, 2014
We spent 6 nights at Suite Aloha at the end of April. The studio apartment was very clean, nicely furnished and decorated in Hawaiian style. We made use of the large gas barbecue...
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From
$5,500
Per Night
10 Bedrooms, 11 Bathrooms, Sleeps 18
37 photos Details Reviews (4) Make Inquiry
From
$345
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details Reviews (7) Make Inquiry
4 of 5 stars Reviewed August 21, 2013
Our family (children age 11 and 9) stayed here for our summer vacation. The location is about as perfect as you can get. A short walk across the lawn right onto one of the most...
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From
$1,950
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 7
22 photos Details Reviews (1) Make Inquiry
From
$195
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
19 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed August 6, 2012
This cabana is in a great location if you are looking for something peaceful and relaxing. We stayed over a weekend after being in Waikiki the week prior, and it was a delightful...
5 of 5 stars Reviewed February 6, 2012
We really enjoyed our short stay at Julie's Cabana. It is beautifully decorated and she made us feel especially welcome with a basket of local goodies and ideas and directions to...
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From
$900
Per Night
5 Bedrooms, 6 Bathrooms, Sleeps 14
24 photos Details Reviews (12) Make Inquiry
From
$145
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
20 photos Details Reviews (16) Make Inquiry
4 of 5 stars Reviewed September 8, 2014
We rented the jungle studio that had one full size bed and a futon. The location is awesome and the room was clean. Located right across the street from Kalapawai Market where...
4 of 5 stars Reviewed May 24, 2014
We were very pleased with our individual units. We had a spacious studio with large closet and great bathroom. Full size fridge but no stove/oven. They did provide a hot plate...
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From
$550
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed April 15, 2014
If you like falling asleep to the sound of the ocean, taking long walks on a soft sand beach or relaxing in the hammock on the lawn, this is the place for you!. Our family of four...
5 of 5 stars Reviewed October 20, 2013
Very nice place for our family since the children are small and can sleep on the couch. The parking is tight. The house is truly right on the beach. A mile from "downtown" Kailua...
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From
$900
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Booking
19 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed April 21, 2014
We just returned from renting this home in Kailua. We were very happy with the home and the owners. The beach was a very short walk and was not crowded at this end. Kailua is a...
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From
$650
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
19 photos Details Reviews (3) Make Inquiry
4 of 5 stars Reviewed January 10, 2014
Lots & lots of room. Family of 7 - 2 kids (8&10), 2 couples & single. So there was plenty of space that we could stay out of each others hair and off each others nerves. We...
5 of 5 stars Reviewed December 19, 2013
Our family of four, my friends family of 5 and my Mom and step father stayed here for 10days. I would recommend it. the beds were comfortable, as was the house. There was no air...
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From
$695
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
26 photos Details Reviews (22) Make Inquiry
5 of 5 stars Reviewed August 25, 2014
This is a lovely and comfortable home, just steps from Kailua Beach, that will give any traveler a wonderful taste of Hawaii. We walked the beach every morning, spent time in the...
5 of 5 stars Reviewed July 7, 2014
We rented the house for a family vacation and to attend our son's wedding wedding. It was everything we could of wanted. No surprises and in excellent condition. Great location...
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From
$100
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details Reviews (29) Make Inquiry
4 of 5 stars Reviewed September 2, 2014
Sharon's Serenity Bed & Breakfast is located within walking distance of beautiful Kailua Beach, one of the nicest beaches we visited while in Hawaii. As promised, Casey the Bichon...
5 of 5 stars Reviewed February 7, 2014
Sharon is a gracious accommodating hostess. She made my stay very pleasant and rejuvenating. I highly recommend her home - she has 2 Bichon dogs who are friendly and quiet. I...
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From
$1,250
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 15
24 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed July 4, 2012
Stayed one week at this beautiful home. Traveled with 7 adults and 2 teens. Everyone had a room and plenty of space. The home is situated so that breeze flow through out the...
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From
$1,250
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
12 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed June 18, 2014
Kailua is a quiet community with a small town feel. It has one the largest most beautiful beaches on Oahu. More peaceful and less crowded than Waikiki. Great hosts at...
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From
$285
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 20
Bookings
26 photos Details Reviews (13) Make Inquiry
4 of 5 stars Reviewed August 25, 2014
Brenda and her co-Horts were so great to work with and very attentive to our needs and request. We had 10 of us and they helped coordinate all the space and rooms we needed to...
5 of 5 stars Reviewed June 11, 2014
We stayed in Palawiki properties with 3-bedroom 2 bath room. The house is spacious , beautiful, lovely and very clean. It is more like a sweet home to my family. The kitchen...
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From
$220
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
18 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed March 26, 2013
This place was just as described, lovely! Peaceful, accommodating and very clean. The owners were very pleasant. We would recommend this place to anyone. It really...
4 of 5 stars Reviewed January 18, 2012
We stayed here for a couple of nights while visiting our son who lives in Kaneohe. The apartment lives up to the pictures shown on TripAdvisor. We were in the one on the ocean...
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From
$330
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
14 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed May 20, 2014
I would highly recommend the Bali House. It had everything that we wanted and needed. It is like staying in your own little resort. The walk to the beach is very easy and...
4 of 5 stars Reviewed April 7, 2014
Bali Hawaii was spacious and nicely appointed. The three of us had plenty of space to spread out and have privacy. What I liked best was the location--a 5 minute walk to the beach...
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From
$139
Per Night
Studio, 1 Bathroom, Sleeps 3
17 photos Details Reviews (21) Make Inquiry
5 of 5 stars Reviewed September 3, 2014
This great little find is located 45 seconds from one of the best beaches in Oahu. It's 5 mins from central Kailua (shops, restaurants, conveniences), and has parking. The place...
5 of 5 stars Reviewed June 2, 2014
Cozy, wonderful studio, best location, just 3 minutes walk from one of the most amazing beaches in the world. Hosts were very helpful and friendly at all times. Looking forward to...
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From
$95
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details Reviews (18) Make Inquiry
5 of 5 stars Reviewed July 3, 2014
The place is a large room for 2 people with AC if you need it. They provide internet service for free. The kitchen is small but will full fill your needs. I would stay here...
5 of 5 stars Reviewed April 23, 2014
We stayed here for 3 days. The studio was clean and very nicely decorated. The small kitchen had everything you would need to cook or prepare meals. Plenty of towels, pillows, and...
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From
$115
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
23 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed August 28, 2014
This studio is very roomy and comfortable with everything needed for a great stay! We did a lot of site seeing on the island, and it was so refreshing to come back to our studio...
4 of 5 stars Reviewed August 10, 2014
We were 4 people (including a 9y old boy) staying 4 nights in this unit. It is nicely located in a quiet area, clean, and well decorated. There's a flat screen TV (we didn't use...
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From
$175
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
11 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed January 31, 2014
We had a wonderful ten-day stay at Maunawili House with our family. The house was spacious, clean and comfortable, and the owners were helpful and welcoming. We loved being...
5 of 5 stars Reviewed October 1, 2013
Maunawili House is comfortable, spacious and well equipped. Beautiful views, quiet, and completely off the beaten path. Close to hiking trails, close enough to beaches, shopping...
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From
$300
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details Reviews (15) Make Inquiry
5 of 5 stars Reviewed March 10, 2014
I have always loved Kailua Beach and the windward side of the island but never stayed there. This bungalow was perfect - easy to find, helpful owners, steps from a path to the...
5 of 5 stars Reviewed April 26, 2012
Having recently returned from our holiday in Hawaii we are so missing Kailua and wish we were back! Our holiday was fantastic the apartment was a great place to stay it...
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From
$115
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
7 photos Details Reviews (19) Make Inquiry
5 of 5 stars Reviewed August 14, 2014
Perfect location away from all the noise of waikiki on in our opinion the best part of Oahu. The local beaches are perfect and Tina is really helpful if you need any info :)
5 of 5 stars Reviewed February 16, 2014
If you want to stay away from Waikiki, try here. Easy walking distance to lovely beaches and everything you need. Make coffee there or take a short stroll to the Kalapawai market...
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From
$825
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
20 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 25, 2014
We loved the Kailua home. The home was well furnished and beautiful. The pool and location was amazing. Sheila (owner) was wonderful to work with and accommodating. If you are...
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From
$160
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
28 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed May 15, 2014
Great & relaxing place to stay, especially sitting in the yard for breakfast, using the BBQ or just hanging around reading and sipping some wine. Reservation is swift, Jenny is...
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From
$4,900
Per Week
6 Bedrooms, 3 Bathrooms, Sleeps 11
16 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 12, 2014
We could not have been happier with this house. It was absolutely perfect for what we wanted, which was time together, easy beach access, fun for all. The house is beach casual...
5 of 5 stars Reviewed April 20, 2014
nice house and property right on kailua beach. perfect beach for the whole family. great boogie boarding, surfing down the way, nice long walks. bike rides into town
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From
$475
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
14 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed August 17, 2014
We stayed here for 7 nights during June of this year. The house was exactly what we were looking for. The location is ideal as it is not more than 1 minute walk from the beach...
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From
$395
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
16 photos Details Reviews (23) Make Inquiry
5 of 5 stars Reviewed April 19, 2014
We wanted to celebrate a 50 year anniversary with the whole family and this proved to be the perfect setting! Each family of 4 had their own 'home': one was in Kukui House...
4 of 5 stars Reviewed November 21, 2013
After 5 weeks travelling in the continental US and Canada with 4 children, we thoroughly enjoyed our week at Kukui House Kailua where we could kick back and relax, enjoy day...
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From
$265
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
13 photos Details Reviews (13) Make Inquiry
3 of 5 stars Reviewed July 14, 2014
First of all, the hosts are friendly and helpful. The location of the villa is very convenient to Kailua Beach. There is also a communal washer and dryer which is very handy to...
5 of 5 stars Reviewed January 21, 2014
Quaint beachy atmosphere. Rooms were clean and well cared for. Charming local decor. Sleeps 4 comfortably. The air conditioner worked perfectly. The kitchen was well stocked with...
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From
$1,325
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
29 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed April 8, 2013
Wonderful location right on the beach and perfect home to celebrate my birthday with all 16 members of my family. Decor was a little dated but adequate. Loved being on the beach...
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From
$275
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 9
23 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed October 9, 2014
Thank you for this wonderful stay, in my language I say, U Siyam, utmost respect of thank you! It was a comfortable little cottage that suit my entire family of 9, WOW! Incredible!
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From
$175
Per Night
Studio, 1 Bathroom, Sleeps 4
Bookings
18 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed September 22, 2014
We loved this wonderful spot. It was as described 5 minutes walk to the beach, beautifully presented, immaculately clean. Eveything we needed was there, they have really thought...
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From
$800
Per Night
8 Bedrooms, 4 Bathrooms, Sleeps 18
18 photos Details Reviews (3) Make Inquiry
4 of 5 stars Reviewed February 19, 2014
On our arrival we were met by Sonya (owner) with cup cakes for the boys. She welcomed us and gave us a tour of her house. House was clean, well decorated, and most of all...
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From
$165
Per Night
Studio, 1 Bathroom, Sleeps 2
Booking
30 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed October 19, 2014
Nancy's Cottage was recommended to us by friends - it was fabulous! My husband, 19yr old daughter and I went to visit our daughter and boyfriend's family. They only lived about...
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From
$150
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
18 photos Details Reviews (9) Make Inquiry
4 of 5 stars Reviewed August 13, 2014
This studio was exactly as advertised and more. It was an easy walk to a beautiful sunrise, supermarkets and restaurants but out of the way enough to avoid the traffic and noise...
5 of 5 stars Reviewed January 8, 2014
This proved a really great choice , the condo is lovely and in a really quiet and peaceful area. Plenty of space and a nice garden with plenty of seating . The owner lives next...
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From
$145
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
32 photos Details Reviews (11) Make Inquiry
5 of 5 stars Reviewed October 9, 2014
We spend some days with our little son at Marias' appartment. It is perfectly equipped and situated very close to the beach. Kailua is a great place to stay with some nice...
5 of 5 stars Reviewed May 3, 2014
My wife an I enjoyed our 5 day stay so much. The area is beautiful and quite compared to Honolulu. The local town has some great places to eat and the people are very friendly...
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From
$95
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
11 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed September 28, 2014
John was an incredible host very resourceful and kind always there whenever my wife or I had a question told us all the good restaurants. Very happy great value, clean, bikes...
3 of 5 stars Reviewed July 6, 2014
Looking for a deal on our Hawaiian getaway, I booked this place after another fell through. I was trying to be thrifty and this looked like it fit our needs. The place is...
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Suitability

  • Wheelchair access (13)
  • Elder access (35)
  • Suitable for children (41)
  • Pet friendly (3)
  • Smoking allowed (0)

Amenities

  • Internet (86)
  • Grill (78)
  • Other outdoor space (71)
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  • Parking (62)
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Book Online(51)

Suitability

  • Wheelchair access (13)
  • Elder access (35)
  • Suitable for children (41)
  • Pet friendly (3)
  • Smoking allowed (0)

Amenities

  • Internet (86)
  • Grill (78)
  • Other outdoor space (71)
  • Washer/Dryer (66)
  • Parking (62)
  • View all amenities
Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.